2,4-Bis(methylsulfanyl)pyrimidine o-quinodimethane: a versatile building block for functionalized fused pyrimidines

Tetrahedron

Volumn 65, Issue 8, 2009, Pages 1697-1703

  Herrera, Antonio ^a   Martínez Álvarez, Roberto ^a   Martín, Nazario ^a   Chioua, Mourad ^a   Chioua, Rachid ^a   Sánchez Vázquez, Ángel ^b   Molero, Dolores ^b   Almy, John ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b Facultad de Química   (Spain)

^c CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

Cycloaddition; Pyrimidine cycloadducts; Pyrimidines; Quinodimethanes

Indexed keywords

2,4 BIS(METHYLSULFANYL) 5,6 DIHYDROCYCLOBUTA[D]PYRIMIDINE; 2,4 BIS(METHYLSULFANYL)PYRIMIDINE 2 QUINODIMETHANE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; PRIORITY JOURNAL; REACTION ANALYSIS;

ALNUS;

EID: 58249098791     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.016     Document Type: Article

References (45)

1. Arnold, D. L.; Moyer, M. P.; Sobolov-Jaynes, S. B. Hung. Pat. Appl. HU 9601559 A2 19970228;
2. Chem. Abstr. 146 (1997) 462275
3. Yonetoku, Y.; Negoro, K.; Onda, K.; Hayakawa, M.; Sasuga, D.; Nigawara, T.; Iikubo, K.; Moritomo, H.; Yoshida, S.; Ohishi, T. WO 2005-JP 18412 20051005;
4. Chem. Abstr. 144 (2005) 412534
5. Yonetoku, Y.; Negoro, K.; Onda, K.; Hayakawa, M.; Sasuga, D.; Nigawara, T.; Iikubo, K.; Moritomo, H.; Yoshida, S.; Ohishi, T. WO 2005-JP19000 20051017;
6. Chem. Abstr. 144 (2005) 422827
7. Fu, Z.; Johnson, M. G.; Li, A-. R.; Marcus, A. P.; Medina, J. C.; Bergeron, P.; Chen, X.; Deignan, J.; Du, X.; Duquette, J. A.; Gustin, D.; Mihalic, J. T. WO 2005-US23251 20050628;
8. Chem. Abstr. 144 (2005) 128993
9. El-Kazi N.A.A., Soleiman H.A., and Khalafallah A.K. Phosphorus, Sulfur Silicon Relat. Elem. 182 (2007) 1459-1473
10. Martín N., and Segura J.L. Chem. Rev. 99 (1999) 3199-3246
11. Collier S.J., and Storr R.C. In: Grible G.W., and Gilchrist T.L. (Eds). Progress in Heterocyclic Chemistry Vol. 10 (1998), Pergamon, New York, NY
12. Chou T.S. Rev. Heteroat. Chem. 8 (1993) 65-104
13. Woyciechowski K. Eur. J. Org. Chem. (2001) 3587-3605
14. Nicolau K.C., Gray D.L.F., and Tae J.S. J. Am. Chem. Soc. 126 (2004) 613-627
15. Clive D.L.J., and Wang J. Org. Prep. Proced. Int. 37 (2005) 1-36
16. Gruber J., Li R.W.C., Aguiar L.H.J.M.C., Benvenho A.R.V., Lessmann R., and Hummelgen I.A. J. Mater. Chem. 15 (2005) 517-522
17. Itoh T., Nomura S., Ohtake M., Yoshida T., Uno T., Kajiwara A., Sada K., and Miyata M. Macromolecules 37 (2004) 8230-8238
18. Yoshida H., Nakano S., Yamaryo Y., Ohshita J., and Kunai A. Org. Lett. 8 (2006) 4157-4159
19. Goli M., Johnston M.R., Margeti D., Schultz A.C., and Warrener R.N. Aust. J. Chem. 59 (2006) 899-914
20. Craig D., Robson M.J., and Shaw S.J. Synlett (1998) 1381-1383
21. Herrera A., Martínez R., González B., Illescas B., Martín N., and Seoane C. Tetrahedron Lett. 38 (1997) 4873-4876
22. Ko C.W., and Chou T.S. Tetrahedron Lett. 30 (1997) 5315-5318
23. Carly P.R., Cappelle S.L., Compernolle F., and Hoornaert G.J. Tetrahedron 52 (1996) 11889-11904
24. Diaz-Ortiz A., Herrero M.A., de la Hoz A., Moreno A., and Carrillo J.R. Synlett (2006) 579-582
25. Tomé J.P.C., Tomé A.C., Neves M., and Cavaleiro J.A.S. Tetrahedron Lett. 38 (1997) 2753-2756
26. Tomé J.P.C., Tomé A.C., Neves M., Almeida P.F.A., Gates P.J., Klinowski J., and Cavaleiro J.A.S. Tetrahedron 59 (2003) 7907-7913
27. Capelle S.L., Vogels I., Compernolle F., and Hoornaert G. Tetrahedron Lett. 42 (2001) 3759-3762
28. Carly P.R., Govaerst T.C., Capelle S.L., and Hoornaert G.J. Tetrahedron 57 (2001) 4203-4212
29. Govaerts T.C., Vogels I., Compernolle F., and Hoornaert G. Tetrahedron 60 (2004) 429-439
30. Herrera A., Martínez-Álvarez R., Chioua M., Chioua R., Almy J., and Sánchez A. Lett. Org. Chem. 3 (2006) 703-708
31. García Martínez A., Herrera A., Moreno F., Luengo M.J., and Subramanian L.R. Synlett (1994) 559-560
32. García Martínez A., Herrera Fernández A., Moreno Jiménez F., Muñoz Martínez P.J., Alonso Martín C., and Subramanian L.R. Tetrahedron 52 (1996) 7973-7982
33. García Martínez A., Herrera Fernández A., Moreno Jiménez F., García Fraile A., Subramanian L.R., and Hanack M. J. Org. Chem. 57 (1992) 1627-1630
34. González B., Herrera A., Illescas B., Martín N., Martínez R., Moreno F., Sánchez L., and Sánchez A. J. Org. Chem. 63 (1998) 6807-6813
35. Di Valentin C., Freccero M., Sarzi-Amadè M., and Zanaletti R. Tetrahedron 56 (2000) 2547-2558
36. Winkler J.D. Chem. Rev. 96 (1996) 167-176
37. Ujaque G., Lee P.S., Houk K.N., and Hentemann M.F. Chem.-Eur. J. 8 (2002) 3423-3430
38. Govaerts T.C., Vogels I.A., Compernolle F., and Hoornaert G.J. Tetrahedron 59 (2003) 5481-5494
39. Govaerts T.C., Vogels I.A., Compernolle F., and Hoornaert G.J. Tetrahedron 60 (2004) 429-439
40. Liu J.-H., Wu A.-T., Huang M.-H., Wu C.-W., and Chung W.-S. J. Org. Chem. 65 (2000) 3395-3403
41. Herrera A., Martínez-Alvarez R., Ramiro P., Molero D., and Almy J. J. Org. Chem. 71 (2006) 3026-3032
42. Herrera A., Martínez-Alvarez R., Ramiro P., and Almy J. Monatsh. Chem. 137 (2006) 1421-1430
43. Herrera A., Martínez-Alvarez R., Ramiro P., Almy J., Molero D., and Sánchez-Vazquez A. Eur. J. Org. Chem. (2006) 3332-3337
44. Stang P.J., Hanack M., and Subramanian L.R. Synthesis (1982) 85-126
45. Stang P.J., and Dueber T.E. Org. Synth. 54 (1974) 79-80